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I was making $27,600 a year. I tried to find another job. I got two offers.

HBO offered me $40k a year. JP Morgan, at the same time, offered me $80K. I turned down JP Morgan.

For two reasons:

  1. I was serious about my freedom.
  2. And I loved HBO. I loved entertainment.

It wasn’t an easy decision, though. Some part of my stomach crumpled up into a knot. It kept asking me these scary questions: “Will you survive?”

“Is that enough?”

“Are you sure?”

“No!” I said. “I’m not sure.”

I’ve never been sure. But I made a choice. And I think I made the right one. If I had taken that job at JP Morgan, I would have been stuck forever being an IT guy somewhere. I would’ve gone crazy.

Steve Cohen gave me this analogy.

He said, “If you put a plant in a jar, it’s going to take the shape of the jar. If you put it in a room, maybe it takes the shape of the whole room. And it blooms even more than you’d ever expect it to bloom.”

I needed to go where I could bloom.

A lot of people think quitting their job and becoming an entrepreneur is the ultimate answer to freedom.

It’s not.

It’s really hard work being an entrepreneur.

When I started my first company, I cried everyday for 15 years. It’s stressful.

For a lot of reasons.

My business would follow me everywhere. I couldn’t leave it at the office.

And there are lot of social problems to worry about too. “Are my employees happy?” “Am I going to make payroll?” You have to work with all these different personalities and at some point two of your employees are going to start having sex with each other. And that’s a liability.

Sometimes being an employee is less of a headache.

And less fear-driving.

But it depends.

There are so many things you can gain being an employee. But you might not be an employee at the right place. (If you’re not sure, remember the plant. Do you have room to grow?)

Steve and I went to the podcast studio and talked about this.

We called the episode “Entrepreneur vs. Employee: They’re Both Great & They Both Suck. Here’s How to Make the Best of Both.”

And I’m going to do more of these on Tuesday’s.

So send me a Tweet or message me on Instagram. Let me know what you think. Or what you want us to talk about next week.